Synthesis of Metabolites and Related Substances of Rabeprazole, an Anti-Ulcerative Drug

Abstract

Rabeprazole sodium (Aciphex®) is a gastric proton pump inhibitor used for the prevention and treatment of gastric acid–related diseases. During the synthesis of bulk drug of rabeprazole sodium, we have observed metabolites rabeprazole sulfide and rabeprazole sulfone and related substances rabeprazole-N-oxide, rabeprazole sulfone-N-oxide, N-aralkyl rabeprazole, chloro rabeprazole, and methoxy rabeprazole as impurities in the drug substance. The present work describes the synthesis and characterization of these compounds.

Keywords:

• Impurities
• metabolites
• rabeprazole Na
• spectral characterization
• synthesis

ACKNOWLEDGMENTS

The authors are grateful to colleagues of the Analytical Research Department of Integrated Product Development Operations, Discovery Research, and the management of Dr. Reddy's Laboratories Ltd. for providing necessary support.

Notes

DRL Communication No. IPDO-IPM-00022